Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights

Vincenzo Marsicano; Antonio Arcadi; Massimiliano Aschi; Marco Chiarini; Giancarlo Fabrizi; Antonella Goggiamani; Fabio Marinelli; Antonia Iazzetti

doi:10.1021/acs.joc.3c00137

Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights

Vincenzo Marsicano, Antonio Arcadi^*, Massimiliano Aschi^*, Marco Chiarini, Giancarlo Fabrizi, Antonella Goggiamani, Fabio Marinelli, Antonia Iazzetti

^*Autore corrispondente per questo lavoro

Risultato della ricerca: Contributo in rivista › Articolo

Abstract

Experimental results and computational insights explain the key role of transition-metal catalysis/Bronsted acid synergism in the achievement of the sequential regioselective direct heteroarylation/ cyclocondensation reactions of beta-(2-aminophenyl)-alpha,beta-ynones with a variety of electron-rich aromatic heterocyclic/arenes to afford quinoline-(hetero)aromatic hybrids. The first approach to the synthesis of 4-(1H-pyrrol-2-yl)quinolines is described. The effectiveness of various transition metals is compared.

Lingua originale	Inglese
pagine (da-a)	6857-6867
Numero di pagine	11
Rivista	Journal of Organic Chemistry
Volume	88
Numero di pubblicazione	11
DOI	https://doi.org/10.1021/acs.joc.3c00137
Stato di pubblicazione	Pubblicato - 2023

All Science Journal Classification (ASJC) codes

Chimica Organica

Keywords

Catalysis
Cyclocondensation Reactions
Transition-metal catalysis

Accesso al documento

10.1021/acs.joc.3c00137

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Marsicano, V., Arcadi, A., Aschi, M., Chiarini, M., Fabrizi, G., Goggiamani, A., Marinelli, F., & Iazzetti, A. (2023). Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights. Journal of Organic Chemistry, 88(11), 6857-6867. https://doi.org/10.1021/acs.joc.3c00137

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title = "Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Br{\o}nsted Acid Synergism: Experimental Results and Computational Insights",

abstract = "Experimental results and computational insights explain the key role of transition-metal catalysis/Bronsted acid synergism in the achievement of the sequential regioselective direct heteroarylation/ cyclocondensation reactions of beta-(2-aminophenyl)-alpha,beta-ynones with a variety of electron-rich aromatic heterocyclic/arenes to afford quinoline-(hetero)aromatic hybrids. The first approach to the synthesis of 4-(1H-pyrrol-2-yl)quinolines is described. The effectiveness of various transition metals is compared.",

keywords = "Catalysis, Cyclocondensation Reactions, Transition-metal catalysis, Catalysis, Cyclocondensation Reactions, Transition-metal catalysis",

author = "Vincenzo Marsicano and Antonio Arcadi and Massimiliano Aschi and Marco Chiarini and Giancarlo Fabrizi and Antonella Goggiamani and Fabio Marinelli and Antonia Iazzetti",

year = "2023",

doi = "10.1021/acs.joc.3c00137",

language = "English",

volume = "88",

pages = "6857--6867",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "11",

}

Marsicano, V, Arcadi, A, Aschi, M, Chiarini, M, Fabrizi, G, Goggiamani, A, Marinelli, F & Iazzetti, A 2023, 'Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights', Journal of Organic Chemistry, vol. 88, n. 11, pagg. 6857-6867. https://doi.org/10.1021/acs.joc.3c00137

Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights. / Marsicano, Vincenzo; Arcadi, Antonio; Aschi, Massimiliano et al.
In: Journal of Organic Chemistry, Vol. 88, N. 11, 2023, pag. 6857-6867.

Risultato della ricerca: Contributo in rivista › Articolo

TY - JOUR

T1 - Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights

AU - Marsicano, Vincenzo

AU - Arcadi, Antonio

AU - Aschi, Massimiliano

AU - Chiarini, Marco

AU - Fabrizi, Giancarlo

AU - Goggiamani, Antonella

AU - Marinelli, Fabio

AU - Iazzetti, Antonia

PY - 2023

Y1 - 2023

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AB - Experimental results and computational insights explain the key role of transition-metal catalysis/Bronsted acid synergism in the achievement of the sequential regioselective direct heteroarylation/ cyclocondensation reactions of beta-(2-aminophenyl)-alpha,beta-ynones with a variety of electron-rich aromatic heterocyclic/arenes to afford quinoline-(hetero)aromatic hybrids. The first approach to the synthesis of 4-(1H-pyrrol-2-yl)quinolines is described. The effectiveness of various transition metals is compared.

KW - Catalysis

KW - Cyclocondensation Reactions

KW - Transition-metal catalysis

KW - Catalysis

KW - Cyclocondensation Reactions

KW - Transition-metal catalysis

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Marsicano V, Arcadi A, Aschi M, Chiarini M, Fabrizi G, Goggiamani A et al. Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights. Journal of Organic Chemistry. 2023;88(11):6857-6867. doi: 10.1021/acs.joc.3c00137